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Literature summary extracted from

  • He, X.; Cane, D.E.
    Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2) (2004), J. Am. Chem. Soc., 126, 2678-2679.
    View publication on PubMed

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.22 2-trans,6-trans-farnesyl diphosphate + H2O Streptomyces coelicolor key step in biosynthesis of geosmin (4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
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?
4.2.3.22 2-trans,6-trans-farnesyl diphosphate + H2O Streptomyces coelicolor A3(2) key step in biosynthesis of geosmin (4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
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Organism

EC Number Organism UniProt Comment Textmining
4.2.3.22 Streptomyces coelicolor
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gene SC9B1.20
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4.2.3.22 Streptomyces coelicolor A3(2)
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gene SC9B1.20
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4.2.3.75 Streptomyces coelicolor
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bifunctional germacradienol/germacrene D synthase
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4.2.3.75 Streptomyces coelicolor A3(2)
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bifunctional germacradienol/germacrene D synthase
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Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.3.22 (2E,6E)-farnesyl diphosphate + H2O = (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate catalytic mechanism via intermediate is (7R)-germacra-1(10),4-diene-11-ol Streptomyces coelicolor
4.2.3.75 (2E,6E)-farnesyl diphosphate = (-)-germacrene D + diphosphate formation of (-)-germacrene D involves a stereospecific 1,3-hydride shift of H-1si of farnesyl diphosphate Streptomyces coelicolor

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.22 2-trans,6-trans-farnesyl diphosphate + H2O key step in biosynthesis of geosmin Streptomyces coelicolor (4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
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?
4.2.3.22 2-trans,6-trans-farnesyl diphosphate + H2O cyclization reaction, detailed mechanism, an intermediate is (7R)-germacra-1(10),4-diene-11-ol Streptomyces coelicolor (4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate GC-MS and NMR product configuration analysis ?
4.2.3.22 2-trans,6-trans-farnesyl diphosphate + H2O key step in biosynthesis of geosmin Streptomyces coelicolor A3(2) (4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
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?
4.2.3.22 2-trans,6-trans-farnesyl diphosphate + H2O cyclization reaction, detailed mechanism, an intermediate is (7R)-germacra-1(10),4-diene-11-ol Streptomyces coelicolor A3(2) (4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate GC-MS and NMR product configuration analysis ?
4.2.3.22 additional information stereospecificity, the 1,3-hydride shift of the (-)-germacrene D synthase of Streptomyces coelicolor A3(2) is opposite to the enzyme from Solidago canadensis Streptomyces coelicolor ?
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?
4.2.3.22 additional information stereospecificity, the 1,3-hydride shift of the (-)-germacrene D synthase of Streptomyces coelicolor A3(2) is opposite to the enzyme from Solidago canadensis Streptomyces coelicolor A3(2) ?
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?
4.2.3.75 (2E,6E)-farnesyl diphosphate
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Streptomyces coelicolor (-)-germacrene D + diphosphate main product is germacradienol, about 15% formation of (-)-(7S)-germacrene ?
4.2.3.75 (2E,6E)-farnesyl diphosphate
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Streptomyces coelicolor A3(2) (-)-germacrene D + diphosphate main product is germacradienol, about 15% formation of (-)-(7S)-germacrene ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.22 germacradienol/germacrene D synthase
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Streptomyces coelicolor